5-(3-pyridyl)-10,15,20-tri-p-tolylporphyrin | 57412-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 5-(3-pyridyl)-10,15,20-tri-p-tolylporphyrin
• 英文别名: 5-pyridin-3-yl-10,15,20-tri-p-tolyl-21H,23H-porphine
• CAS: 57412-10-9
• 化学式: C₄₆H₃₅N₅
• 分子量: 657.817
• InChiKey: VXHQGIQBZFLPBK-CRLDETFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.64
• 重原子数：
  51.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.25
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2,3,7,8,12,13,17,18-octaethylporphyrinato)zinc(II) 、 5-(3-pyridyl)-10,15,20-tri-p-tolylporphyrin 在 tetraethylammonium hexafluorophosphate 、 2,6-lutidine 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 以85%的产率得到
  参考文献：
  名称：

  以吡啶鎓为桥间隔基的卟啉二聚体的电合成和电化学性质

  摘要：

  二 卟啉通过控制电位电解已获得了具有吡啶鎓作为桥间隔基的二聚体（更确切地说是两个异构体）。该方法基于被吡啶基取代的卟啉的亲核取代（即5,10,15-三甲苯基-20-（4-吡啶基）卟啉（H 2 T 3 P-4-Py）或5,10,15-三甲苯基-20-（3-吡啶基）卟啉（H 2 T 3 P-3-Py））在β-八乙基卟啉锌（ZnOEP）的电产生的自由基阳离子上。这些新化合物已通过HR-MS，1 H NMR，UV-vis和荧光光谱进行了表征。还讨论了两个二聚体之间吡啶鎓间隔基的电化学行为的差异。

  DOI：

  10.1039/c1nj20177h
• 作为产物：
  描述：

  3-吡啶甲醛 、 吡咯 、 对甲基苯甲醛 在 丙酸 作用下， 反应 3.5h， 以920 mg的产率得到5-(3-pyridyl)-10,15,20-tri-p-tolylporphyrin
  参考文献：
  名称：

  Synthesis and Properties of 5-(3-Pyridyl)porphyrinatoruthenium(II) Tetramers

  摘要：

  5-(3-吡啶基)卟啉钌(II)四聚体, [{Ru(3-PyT3porph)(CO)}4] (1), [{Ru(3-PytB3porph)(CO)}4] (2), [制备{Ru(3-PyHex3porph)(CO)}4](3)和[{Ru(3-PytB3porph)(py)}4](4)。通过 1 H NMR、IR 和 ESI-MS 测量，分离出的四聚体的结构被确定为菱形，具有两个化学上不等价的卟啉钌 (II) 亚基。四聚体在 70 °C 的苯中稳定。然而，通过 1 H NMR 光谱法观察到，四聚体在室温下在二氯甲烷中与大量过量的吡啶反应，得到卟啉钌(II)的两种几何异构体。四聚体的紫外可见光谱显示，由于激子相互作用，索雷带分裂或展宽。在循环伏安图中观察到环状四聚体骨架中的卟啉环或钌离子的逐步氧化。

  DOI：

  10.1246/bcsj.80.1556

文献信息

• Effect of configuration of viologen-linked porphyrin on photocurrent generation and on photoinduced hydrogen evolution
  作者：Hideyuki Hosono、Masao Kaneko

  DOI：10.1039/a607494d

  日期：——

  Two types of viologen-linked porphyrin with different configuration between the porphyrin and the bonded viologen have been synthesized and Langmuir–Blodgett (LB) films prepared. The effects of the different configurations on the photoelectric conversion by indium tin oxide (ITO) electrodes modified with the LB films and on photoinduced hydrogen evolution, using the LB films and H 2 PtCl 6 as a catalyst in the presence of ethylenediaminetetraacetic acid (EDTA) as a sacrificial electron donor, have been investigated. No effect was detected for the photocurrent generation but photoinduced hydrogen evolution was dependent upon the configuration. These results show that the rate of diffusion of small electrolyte ions is the same in both LB films but diffusion of large EDTA molecules is affected by the configuration. Hence, the molecular structure of viologen-linked porphyrin must be taken into account in order to make diffusion of reactant in the LB film easy and thus to increase the reaction yield.

  两种卟啉与结合的紫精素之间具有不同构型（porphyrin and the bonded viologen have been synthesized）的紫精素连接卟啉已经合成，并制备了Langmuir-Blodgett（LB）薄膜。研究不同构型对铟锡氧化物（ITO）电极的光电转换的影响（通过LB薄膜修饰），以及光诱导的氢化反应（使用LB薄膜和H2PtCl6作为催化剂，在乙二胺四乙酸（EDTA）作为牺牲电子供体的情况下）。没有检测到对光电流产生的影响，但光诱导的氢化反应取决于构型。这些结果表明，两种LB薄膜中小电解质离子的扩散速率相同，但大EDTA分子的扩散受构型的影响。因此，必须考虑紫精素连接卟啉的分子结构，以使反应物在LB薄膜中的扩散更容易，从而提高反应产率。
• Design and synthesis of charged porphyrin dimers for polyoxometalate recognition
  作者：Raphaël Lamare、Romain Ruppert、Mourad Elhabiri、Gilles Ulrich、Laurent Ruhlmann、Jean Weiss

  DOI：10.5802/crchim.105

  日期：——
• Photoinduced intramolecular electron transfer in viologen-linked zinc porphyrins in dimethyl sulfoxide
  作者：Ichiro Okura、Hideyuki Hosono

  DOI：10.1021/j100190a063

  日期：1992.5

  Compounds containing a viologen linked to a zinc porphyrin via methylene groups have been synthesized, and photoinduced intramolecular electron transfer between porphyrin and viologen was observed. The photoexcited singlet state of the porphyrin was quenched by the bonded viologen, the photoexcited triplet state was quenched, and the lifetime of the charge separated species was about 1-mu-s.
• Formation of a new hybrid complex via coordination interaction between 5,10,15-tritolyl-20-(4- and 3-pyridyl)porphyrin or 5,10,15-triphenyl-20-(4-pyridyl)porphyrin and the α-[MSiW11O39]6− Keggin-type polyoxometalate (M=Co2+ and Ni2+)
  作者：D. Schaming、C. Costa-Coquelard、I. Lampre、S. Sorgues、M. Erard、X. Liu、J. Liu、L. Sun、J. Canny、R. Thouvenot、L. Ruhlmann

  DOI：10.1016/j.ica.2010.03.015

  日期：2010.6

  New complexes based on a coordination interaction between a pyridyl-porphyrin (namely 5,10,15-tritolyl-20-(4-pyridyl)porphyrin, 5,10,15-tritolyl-20-(3-pyridyl)porphyrin or 5,10,15-triphenyl-20-(4-pyridyl)porphyrin) and a Keggin-type polyoxometalate (alpha-[MSiW11O39](6-), M=Co2+ or Ni2+) are formed in solution. The formation of these complexes is clearly evidenced by steady-state and time-resolved luminescence measurements. A strong quenching of the porphyrin fluorescence, accompanied by an important shortening of the fluorescence lifetime, is observed upon addition of the POM and formation of the complexes. Using a variant of the Job's method from the luminescence spectra, the association constants of the complexes have been estimated to be around 10(6) L mol(-1). Paramagnetic H-1 NMR experiments confirm the formation of the complexes. Indeed, in addition to broadenings of the signals, the coordination binding of the POM to the porphyrin induces large high-frequency shifts for the protons of the pyridyl group coordinated to the paramagnetic metal, and low-frequency shifts for all the other resonances. (C) 2010 Elsevier B.V. All rights reserved.
• ¹H NMR Conformational Study of Viologen-Linked Porphyrins
  作者：Yasuhiko Yamamoto、Sumio Noda、Norishige Nanai、Ichiro Okura、Yoshio Inoue

  DOI：10.1246/bcsj.62.2152

  日期：1989.7

  Novel porphyrins to which the viologen is linked (m-PCnV) were synthesized. The linkage methylene chain between the porphyrin and the bipyridine moieties was systematically changed from (CH2)3 to (CH2)6. The molecular structure of m-PCnV was characterized by 1H NMR in some detail. The orientation of the viologen with respect to the porphyrin plane in m-PCnV was semiquantitatively estimated from the porphyrin ring current induced chemical shift changes on the resonances from the viologen moiety. The NMR conformational analyses on m-PCnV in dimethyl sulfoxide and acetonitrile clearly revealed the effect of the solvent on its molecular structure.